Hydrogen Bromide → 2(3-Aminopropylthio)imidazole dihydrobromide

Participants

Reaction Steps

A solution of 2-mercaptoimidazole (2 g.) and 3-aminopropanol (1.14 ml.) in hydrobromic acid (48%, 25 ml.) was heated under reflux for 25 hours. The reaction mixture was evaporated to dryness and the oily residue solid recrystallised twice from ethanol/ether to give 2-(3-aminopropylmercapto)imidazole dihydrobromide (3.55 g.) m.p. 160°-162°. (ii) This amine dihydrobromide (7 g.) was converted to the free base and reacted with methyl isothiocyanate (1.75 g.), by the method described in Example 1 (ii), to give a crude yellow solid after evaporation of the reaction mixture. This crude product was washed with acetone/isopropyl acetate (1.1) and recrystallised from water to give N-methyl-N'-[3-(2-imidazolylthio)propyl]thiourea (3.46 g.) m.p. 139°-141°. (Found: C, 41.5; H, 6.1; N, 24.1; S, 27.7. C8H14N4S2 requires: C, 41.7; H, 6.1; N, 24.3; S, 27.8).

Provenance & Evidence